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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:37 UTC
HMDB IDHMDB0014442
Secondary Accession Numbers
  • HMDB14442
Metabolite Identification
Common NameBupivacaine
DescriptionBupivacaine is only found in individuals that have used or taken this drug. It is a widely used local anesthetic agent. [PubChem]Bupivacaine blocks the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. Bupivacaine binds to the intracellular portion of sodium channels and blocks sodium influx into nerve cells, which prevents depolarization. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers. Clinically, the order of loss of nerve function is as follows: (1) pain, (2) temperature, (3) touch, (4) proprioception, and (5) skeletal muscle tone. The analgesic effects of Bupivicaine are thought to potentially be due to its binding to the prostaglandin E2 receptors, subtype EP1 (PGE2EP1), which inhibits the production of prostaglandins, thereby reducing fever, inflammation, and hyperalgesia.
Structure
Data?1582753180
Synonyms
ValueSource
BupivacainaChEBI
BupivacainumChEBI
DL-BupivacaineChEBI
MarcaineChEBI
BucaineKegg
ExparelKegg
(+-)-BupivacaineHMDB
BloqueinaHMDB
Bupivacaine HCLHMDB
Bupivacaine HCL kitHMDB
CBupivacaineHMDB
DUR-843HMDB
LAC-43HMDB
Braun, bupivacainaMeSH, HMDB
Bupivacaine carbonateMeSH, HMDB
Bupivacaine monohydrochloride, monohydrateMeSH, HMDB
Strathmann brand OF bupivacaine hydrochlorideMeSH, HMDB
Abbott brand OF bupivacaine hydrochlorideMeSH, HMDB
Astra brand OF bupivacaine hydrochlorideMeSH, HMDB
CarbostesinMeSH, HMDB
DolanaestMeSH, HMDB
Inibsa brand OF bupivacaine hydrochlorideMeSH, HMDB
Janapharm, bupivacainMeSH, HMDB
1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamideMeSH, HMDB
Anhydrous, bupivacaineMeSH, HMDB
Bupivacain janapharmMeSH, HMDB
Bupivacain-RPRMeSH, HMDB
Bupivacaina braunMeSH, HMDB
Bupivacaine anhydrousMeSH, HMDB
Bupivacaine hydrochlorideMeSH, HMDB
Carbonate, bupivacaineMeSH, HMDB
Jenapharm brand OF bupivacaine hydrochlorideMeSH, HMDB
SensorcaineMeSH, HMDB
AstraZeneca brand OF bupivacaine hydrochlorideMeSH, HMDB
Aventis brand OF bupivacaine hydrochlorideMeSH, HMDB
Braun brand OF bupivacaine hydrochlorideMeSH, HMDB
Bupivacain RPRMeSH, HMDB
BuvacainaMeSH, HMDB
Hydrochloride, bupivacaineMeSH, HMDB
MarcainMeSH, HMDB
Pisa brand OF bupivacaine hydrochlorideMeSH, HMDB
Svedocain sin vasoconstrMeSH, HMDB
Chemical FormulaC18H28N2O
Average Molecular Weight288.4277
Monoisotopic Molecular Weight288.220163528
IUPAC Name1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
Traditional Namebupivacaine
CAS Registry Number2180-92-9
SMILES
CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C
InChI Identifier
InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)
InChI KeyLEBVLXFERQHONN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • 2-piperidinecarboxamide
  • Piperidinecarboxamide
  • Anilide
  • M-xylene
  • Xylene
  • N-arylamide
  • Monocyclic benzene moiety
  • Benzenoid
  • Piperidine
  • Carboxamide group
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point107 - 108 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.098 g/LNot Available
LogP3.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM173.130932474
[M+H]+Not Available171.619http://allccs.zhulab.cn/database/detail?ID=AllCCS00001291
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.098 g/LALOGPS
logP3.31ALOGPS
logP4.52ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity90.19 m³·mol⁻¹ChemAxon
Polarizability34.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.44631661259
DarkChem[M-H]-166.74931661259
DeepCCS[M+H]+174.28530932474
DeepCCS[M-H]-171.92730932474
DeepCCS[M-2H]-204.81330932474
DeepCCS[M+Na]+180.37830932474
AllCCS[M+H]+172.832859911
AllCCS[M+H-H2O]+169.532859911
AllCCS[M+NH4]+175.832859911
AllCCS[M+Na]+176.732859911
AllCCS[M-H]-174.732859911
AllCCS[M+Na-2H]-175.232859911
AllCCS[M+HCOO]-175.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BupivacaineCCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C2726.9Standard polar33892256
BupivacaineCCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C2317.2Standard non polar33892256
BupivacaineCCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C2280.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bupivacaine,1TMS,isomer #1CCCCN1CCCCC1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C2163.0Semi standard non polar33892256
Bupivacaine,1TMS,isomer #1CCCCN1CCCCC1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C2224.1Standard non polar33892256
Bupivacaine,1TMS,isomer #1CCCCN1CCCCC1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C2862.7Standard polar33892256
Bupivacaine,1TBDMS,isomer #1CCCCN1CCCCC1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2383.9Semi standard non polar33892256
Bupivacaine,1TBDMS,isomer #1CCCCN1CCCCC1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2453.3Standard non polar33892256
Bupivacaine,1TBDMS,isomer #1CCCCN1CCCCC1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2963.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bupivacaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-6920000000-20e4e8d5c09a52a31c752017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bupivacaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bupivacaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupivacaine LC-ESI-QFT , positive-QTOFsplash10-000i-0290000000-c1dbebb634be5e7e11402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupivacaine LC-ESI-QFT , positive-QTOFsplash10-0006-0910000000-ae34de204bcb9a9deb232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupivacaine LC-ESI-QFT , positive-QTOFsplash10-0006-0900000000-7ea7001506aae0c271a02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupivacaine LC-ESI-QFT , positive-QTOFsplash10-0006-2900000000-ef819c5e235d6d524d8c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupivacaine LC-ESI-QFT , positive-QTOFsplash10-0006-7900000000-22d7491053c05d773e932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupivacaine LC-ESI-QFT , positive-QTOFsplash10-001l-9400000000-71357b8186126c5933ce2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupivacaine 90V, Positive-QTOFsplash10-001l-9400000000-f152216f702642a2a96b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupivacaine 15V, Positive-QTOFsplash10-000i-0290000000-473772a88887df5462f72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupivacaine 45V, Positive-QTOFsplash10-0006-0900000000-73c58abee6a70ae243ed2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupivacaine 30V, Positive-QTOFsplash10-0006-0910000000-2d35aaa0fbbc69b60c7d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupivacaine 60V, Positive-QTOFsplash10-0006-2900000000-c1144b59f68c252397712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupivacaine 75V, Positive-QTOFsplash10-0006-7900000000-a4b8408dc9df272675892021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupivacaine 10V, Positive-QTOFsplash10-0079-0970000000-e665f05dc8da9fafd8f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupivacaine 20V, Positive-QTOFsplash10-00dl-2900000000-6396ddc6fc9d5e9b6c642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupivacaine 40V, Positive-QTOFsplash10-0ac0-9200000000-befeaee90e72918d68b32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupivacaine 10V, Negative-QTOFsplash10-000i-0290000000-e01610a30f93d9c5ec2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupivacaine 20V, Negative-QTOFsplash10-00ri-0970000000-e26949f880557c6da8152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupivacaine 40V, Negative-QTOFsplash10-00xr-3900000000-56dfe5d9cd7f629f17e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupivacaine 10V, Negative-QTOFsplash10-000i-0090000000-e83ab5b70775090159b72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupivacaine 20V, Negative-QTOFsplash10-000i-0690000000-6ff0193988455d2867262021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupivacaine 40V, Negative-QTOFsplash10-00xr-1920000000-87f1897c4a60793791d52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupivacaine 10V, Positive-QTOFsplash10-000i-0190000000-23ffc5622396245151832021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupivacaine 20V, Positive-QTOFsplash10-000g-3920000000-6aaf7d8f5f0149cec33e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupivacaine 40V, Positive-QTOFsplash10-0007-8900000000-e62af4b8065c6c1caf012021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00297 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00297 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00297
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2380
KEGG Compound IDC07529
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBupivacaine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID77431
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9. [PubMed:16430560 ]
  2. Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB: Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology. 2006 Jul;105(1):217-8. [PubMed:16810015 ]
  3. eMedicine [Link]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Gantenbein M, Attolini L, Bruguerolle B, Villard PH, Puyoou F, Durand A, Lacarelle B, Hardwigsen J, Le-Treut YP: Oxidative metabolism of bupivacaine into pipecolylxylidine in humans is mainly catalyzed by CYP3A. Drug Metab Dispos. 2000 Apr;28(4):383-5. [PubMed:10725304 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an important modulator of renal function. Implicated the smooth muscle contractile response to PGE2 in various tissues
Gene Name:
PTGER1
Uniprot ID:
P34995
Molecular weight:
41800.7
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Beloeil H, Gentili M, Benhamou D, Mazoit JX: The effect of a peripheral block on inflammation-induced prostaglandin E2 and cyclooxygenase expression in rats. Anesth Analg. 2009 Sep;109(3):943-50. doi: 10.1213/ane.0b013e3181aff25e. [PubMed:19690271 ]
General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
Molecular weight:
220623.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Sheets MF, Fozzard HA, Lipkind GM, Hanck DA: Sodium channel molecular conformations and antiarrhythmic drug affinity. Trends Cardiovasc Med. 2010 Jan;20(1):16-21. doi: 10.1016/j.tcm.2010.03.002. [PubMed:20685573 ]